JPWO2019191092A5 - - Google Patents
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- Publication number
- JPWO2019191092A5 JPWO2019191092A5 JP2020552026A JP2020552026A JPWO2019191092A5 JP WO2019191092 A5 JPWO2019191092 A5 JP WO2019191092A5 JP 2020552026 A JP2020552026 A JP 2020552026A JP 2020552026 A JP2020552026 A JP 2020552026A JP WO2019191092 A5 JPWO2019191092 A5 JP WO2019191092A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazine
- amino
- phenol
- pyrazole
- tetramethylpiperidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 1,2-dihydropyridinyl Chemical group 0.000 claims 93
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims 1
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims 1
- IKNUIKBFNNJXQD-UHFFFAOYSA-N 2-(5-piperidin-4-yloxypyrazin-2-yl)-5-(1H-pyrazol-4-yl)phenol Chemical compound N1CCC(CC1)OC=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O IKNUIKBFNNJXQD-UHFFFAOYSA-N 0.000 claims 1
- OASPCOJIXLTDNU-UHFFFAOYSA-N 2-(5-piperidin-4-yloxypyrazin-2-yl)-5-(1H-pyrazol-4-yl)phenol trihydrochloride Chemical compound Cl.Cl.Cl.N1CCC(CC1)OC=1N=CC(=NC1)C1=C(C=C(C=C1)C=1C=NNC1)O OASPCOJIXLTDNU-UHFFFAOYSA-N 0.000 claims 1
- DIGMVIFWRARWAA-UHFFFAOYSA-N 2-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazine Chemical compound FC1=C(C=CC(=C1F)C=1C=NNC=1)C1=NC=C(N=C1)OC1CC(NC(C1)(C)C)(C)C DIGMVIFWRARWAA-UHFFFAOYSA-N 0.000 claims 1
- DZQBYXJNUAVIBZ-UHFFFAOYSA-N 2-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazine trihydrochloride Chemical compound CC1(CC(CC(N1)(C)C)OC2=NC=C(N=C2)C3=C(C(=C(C=C3)C4=CNN=C4)F)F)C.Cl.Cl.Cl DZQBYXJNUAVIBZ-UHFFFAOYSA-N 0.000 claims 1
- PGJONQZOJFKMDI-UHFFFAOYSA-N 2-[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1N(CC2C1CNC2)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O PGJONQZOJFKMDI-UHFFFAOYSA-N 0.000 claims 1
- AQPVVBVWDFPJIS-UHFFFAOYSA-N 2-[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol tetrahydrochloride Chemical compound C1C2CN(CC2CN1)C3=NC=C(N=C3)C4=C(C=C(C=C4)C5=CNN=C5)O.Cl.Cl.Cl.Cl AQPVVBVWDFPJIS-UHFFFAOYSA-N 0.000 claims 1
- GGRSYZQGVRWXPJ-UHFFFAOYSA-N 2-[5-(2,7-diazaspiro[3.4]octan-2-yl)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C1N(CC11CNCC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O GGRSYZQGVRWXPJ-UHFFFAOYSA-N 0.000 claims 1
- ZZCFEUQEEVGWKB-UHFFFAOYSA-N 2-[5-(piperidin-4-ylamino)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound N1CCC(CC1)NC=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O ZZCFEUQEEVGWKB-UHFFFAOYSA-N 0.000 claims 1
- GSDATBBMDNCKCT-UHFFFAOYSA-N 2-[5-(piperidin-4-ylamino)pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol tetrahydrochloride Chemical compound C1CNCCC1NC2=NC=C(N=C2)C3=C(C=C(C=C3)C4=CNN=C4)O.Cl.Cl.Cl.Cl GSDATBBMDNCKCT-UHFFFAOYSA-N 0.000 claims 1
- DJUDFYVWPSROQV-UHFFFAOYSA-N 2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)N1N=CC=N1 DJUDFYVWPSROQV-UHFFFAOYSA-N 0.000 claims 1
- OZYCXOXQSURAGX-UHFFFAOYSA-N 2-[5-[2-hydroxy-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]-2-(2,2,6,6-tetramethylpiperidin-4-yl)acetonitrile Chemical compound OC1=C(C=CC(=C1)C=1C=NNC=1)C=1N=CC(=NC=1)C(C#N)C1CC(NC(C1)(C)C)(C)C OZYCXOXQSURAGX-UHFFFAOYSA-N 0.000 claims 1
- HHTJEPSYVJFJSQ-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O HHTJEPSYVJFJSQ-UHFFFAOYSA-N 0.000 claims 1
- FLYPXFRSCMKLHG-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1-methylpyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.Cn1cc(cn1)-c1ccc(c(O)c1)-c1cnc(cn1)N1CCC(C1)NC(C)(C)C FLYPXFRSCMKLHG-UHFFFAOYSA-N 0.000 claims 1
- YPKUJWIGUBMAOC-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O YPKUJWIGUBMAOC-UHFFFAOYSA-N 0.000 claims 1
- MJBABKMSSYHMCO-UHFFFAOYSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 MJBABKMSSYHMCO-UHFFFAOYSA-N 0.000 claims 1
- HHTJEPSYVJFJSQ-GKOSEXJESA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(C)(C)(C)NC1CN(CC1)C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NN(C=1)C([2H])([2H])[2H])O HHTJEPSYVJFJSQ-GKOSEXJESA-N 0.000 claims 1
- FLYPXFRSCMKLHG-DULOSRJUSA-N 2-[5-[3-(tert-butylamino)pyrrolidin-1-yl]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol dihydrochloride Chemical compound Cl.Cl.[2H]C([2H])([2H])n1cc(cn1)-c1ccc(c(O)c1)-c1cnc(cn1)N1CCC(C1)NC(C)(C)C FLYPXFRSCMKLHG-DULOSRJUSA-N 0.000 claims 1
- SVZIYQDLLKCYFU-UHFFFAOYSA-N 2-[5-[amino-(2,2,6,6-tetramethylpiperidin-4-yl)methyl]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound NC(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C SVZIYQDLLKCYFU-UHFFFAOYSA-N 0.000 claims 1
- FKEBCGSHHBRTPF-UHFFFAOYSA-N 2-[5-[methyl(piperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CCNCC1 FKEBCGSHHBRTPF-UHFFFAOYSA-N 0.000 claims 1
- KYLQBJVOMJMWGU-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol hydrobromide Chemical compound Br.CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 KYLQBJVOMJMWGU-UHFFFAOYSA-N 0.000 claims 1
- XXCBCHUIECDYDQ-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=CC=N1)O)C1CC(NC(C1)(C)C)(C)C XXCBCHUIECDYDQ-UHFFFAOYSA-N 0.000 claims 1
- CJBAWWOUMQLVHW-VPYROQPTSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-[1-(trideuteriomethyl)pyrazol-4-yl]phenol Chemical compound C(N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)([2H])([2H])[2H] CJBAWWOUMQLVHW-VPYROQPTSA-N 0.000 claims 1
- NXJUVYCMVOOVJT-UHFFFAOYSA-N 2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-pyrazol-1-ylphenol Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=CC=C1)O)C1CC(NC(C1)(C)C)(C)C NXJUVYCMVOOVJT-UHFFFAOYSA-N 0.000 claims 1
- AIPSUZCQFPSGLV-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-1H-pyrazole-5-carbonitrile Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NNC=1C#N AIPSUZCQFPSGLV-UHFFFAOYSA-N 0.000 claims 1
- GTAYBMVFMPMRCY-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-1H-pyridin-2-one Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C1=CC(=NC=C1)O GTAYBMVFMPMRCY-UHFFFAOYSA-N 0.000 claims 1
- NAGODULBRRMYTM-UHFFFAOYSA-N 4-[3-hydroxy-4-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl]-2-methylpyrazole-3-carbonitrile Chemical compound OC=1C=C(C=CC=1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NN(C=1C#N)C NAGODULBRRMYTM-UHFFFAOYSA-N 0.000 claims 1
- BYRFQNHNCDBMBE-UHFFFAOYSA-N 4-fluoro-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound FC1=CC(=C(C=C1C=1C=NNC=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C BYRFQNHNCDBMBE-UHFFFAOYSA-N 0.000 claims 1
- ZVLBHUOHQNYWPZ-UHFFFAOYSA-N 4-fluoro-5-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-2-(1H-pyrazol-4-yl)benzonitrile Chemical compound FC1=CC(=C(C#N)C=C1C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C)C=1C=NNC=1 ZVLBHUOHQNYWPZ-UHFFFAOYSA-N 0.000 claims 1
- CMDFZHYVQPQELQ-UHFFFAOYSA-N 5-(1,5-dimethylpyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1C)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C CMDFZHYVQPQELQ-UHFFFAOYSA-N 0.000 claims 1
- PQWKSBIYLLJDAM-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PQWKSBIYLLJDAM-UHFFFAOYSA-N 0.000 claims 1
- CJBAWWOUMQLVHW-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C CJBAWWOUMQLVHW-UHFFFAOYSA-N 0.000 claims 1
- MCYFRMAVSYYRBB-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazin-2-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)OC1CC(NC(C1)(C)C)(C)C MCYFRMAVSYYRBB-UHFFFAOYSA-N 0.000 claims 1
- QUOQPMKZWUYSKF-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-(2,2,6,6-tetramethylpiperidin-4-yl)oxypyrazin-2-yl]phenol hydrochloride Chemical compound Cl.CC1(C)CC(CC(C)(C)N1)Oc1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1 QUOQPMKZWUYSKF-UHFFFAOYSA-N 0.000 claims 1
- DUMYCWDXIVSOQM-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1N=CC(=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C DUMYCWDXIVSOQM-UHFFFAOYSA-N 0.000 claims 1
- LGHAGLPDIOJZSQ-UHFFFAOYSA-N 5-(1H-pyrazol-5-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-c1ccn[nH]1 LGHAGLPDIOJZSQ-UHFFFAOYSA-N 0.000 claims 1
- LMFIWTZDOGYPQO-UHFFFAOYSA-N 5-(3-aminopyrazol-1-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound NC1=NN(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C LMFIWTZDOGYPQO-UHFFFAOYSA-N 0.000 claims 1
- DNADVCPATWWFGM-UHFFFAOYSA-N 5-(4-fluoropyrazol-1-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-n1cc(F)cn1 DNADVCPATWWFGM-UHFFFAOYSA-N 0.000 claims 1
- LNZKMSFMFQYFAO-UHFFFAOYSA-N 5-(5-chloro-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound ClC1=C(C=NN1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C LNZKMSFMFQYFAO-UHFFFAOYSA-N 0.000 claims 1
- UQMXADBFKHOXAR-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1O)-c1cn[nH]c1F UQMXADBFKHOXAR-UHFFFAOYSA-N 0.000 claims 1
- PHFTVBJWFCBELW-UHFFFAOYSA-N 5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound FC1=NNC=C1C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C PHFTVBJWFCBELW-UHFFFAOYSA-N 0.000 claims 1
- VTYVULOWLCPDAE-UHFFFAOYSA-N 5-(5-methyl-1H-pyrazol-4-yl)-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1=C(C=NN1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)N(C1CC(NC(C1)(C)C)(C)C)C VTYVULOWLCPDAE-UHFFFAOYSA-N 0.000 claims 1
- PXCHKBILLARLLX-UHFFFAOYSA-N 5-(6-methoxypyrimidin-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound COC1=CC(=NC=N1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PXCHKBILLARLLX-UHFFFAOYSA-N 0.000 claims 1
- WBWIUOYKHMWYFU-UHFFFAOYSA-N 5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=CC(=C1F)C=1C=NNC=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C WBWIUOYKHMWYFU-UHFFFAOYSA-N 0.000 claims 1
- XJWLUMIGMIGLLC-UHFFFAOYSA-N 5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine hydrochloride Chemical compound Cl.CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(-c2cn[nH]c2)c(F)c1F XJWLUMIGMIGLLC-UHFFFAOYSA-N 0.000 claims 1
- XSUNNOLPPMCQNM-UHFFFAOYSA-N 5-[2,3-difluoro-4-(4-methylimidazol-1-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=CC(=C1F)N1C=NC(=C1)C)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C XSUNNOLPPMCQNM-UHFFFAOYSA-N 0.000 claims 1
- BEMFMPBESBUDOW-UHFFFAOYSA-N 5-[2,5-dichloro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound ClC1=C(C=C(C(=C1)C=1C=NNC=1)Cl)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C BEMFMPBESBUDOW-UHFFFAOYSA-N 0.000 claims 1
- ZVTDOQWCYFJQAL-UHFFFAOYSA-N 5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=C(C(=C1)C=1C=NNC=1)F)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C ZVTDOQWCYFJQAL-UHFFFAOYSA-N 0.000 claims 1
- GQXWQGYXNSISOF-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC1=C(C=C(C(=C1)C=1C=NNC=1)C)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C GQXWQGYXNSISOF-UHFFFAOYSA-N 0.000 claims 1
- ZNFRTMGFKOPSIR-UHFFFAOYSA-N 5-[3,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC=1C=C(C=C(C=1C=1C=NNC=1)F)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C ZNFRTMGFKOPSIR-UHFFFAOYSA-N 0.000 claims 1
- NIBRAOVIPJXQHW-UHFFFAOYSA-N 5-[3-fluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound FC=1C=C(C=CC=1C=1C=NNC=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C NIBRAOVIPJXQHW-UHFFFAOYSA-N 0.000 claims 1
- QFBTZAZRFWCMTG-UHFFFAOYSA-N 5-[5-chloro-2-fluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrazin-2-amine Chemical compound ClC=1C(=CC(=C(C=1)C=1N=CC(=NC=1)N(C1CC(NC(C1)(C)C)(C)C)C)F)C=1C=NNC=1 QFBTZAZRFWCMTG-UHFFFAOYSA-N 0.000 claims 1
- AAJPZNKNQJJTKH-UHFFFAOYSA-N 5-imidazo[1,2-a]pyrazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)C1=CN2C=CN=C2C=N1 AAJPZNKNQJJTKH-UHFFFAOYSA-N 0.000 claims 1
- YOURWMUJBGHWJG-UHFFFAOYSA-N 5-imidazo[1,2-b]pyridazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(O)C=C(C=C1)C1=NN2C=CN=C2C=C1 YOURWMUJBGHWJG-UHFFFAOYSA-N 0.000 claims 1
- HPEBYVKMECBKSL-UHFFFAOYSA-N 5-imidazol-1-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1(C=NC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C HPEBYVKMECBKSL-UHFFFAOYSA-N 0.000 claims 1
- RTELLJFZTFWNSE-UHFFFAOYSA-N 5-imidazol-1-yl-2-[5-[methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound CN(C1CC(C)(C)NC(C)(C)C1)c1cnc(cn1)-c1ccc(cc1O)-n1ccnc1 RTELLJFZTFWNSE-UHFFFAOYSA-N 0.000 claims 1
- ZCILNELTDVTXEM-UHFFFAOYSA-N 5-pyridin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=C(C=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C ZCILNELTDVTXEM-UHFFFAOYSA-N 0.000 claims 1
- GSNOMESXIOXXJF-UHFFFAOYSA-N 5-pyridin-3-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=CC(=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C GSNOMESXIOXXJF-UHFFFAOYSA-N 0.000 claims 1
- PHVQAAMYKMYCFZ-UHFFFAOYSA-N 5-pyridin-4-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=CC=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C PHVQAAMYKMYCFZ-UHFFFAOYSA-N 0.000 claims 1
- KLRZPNFBFXYMIL-UHFFFAOYSA-N 5-pyrimidin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenol Chemical compound N1=C(N=CC=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C KLRZPNFBFXYMIL-UHFFFAOYSA-N 0.000 claims 1
- XXHJACUVXZBAHX-UHFFFAOYSA-N CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C Chemical compound CN(C=1N=CC(=NC=1)C1=C(C=C(C=C1)C=1C=NNC=1)O)C1CC(NC(C1)(C)C)(C)C XXHJACUVXZBAHX-UHFFFAOYSA-N 0.000 claims 1
- RFYNOSZOQAMUOK-UHFFFAOYSA-N CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C Chemical compound CN1N=C(C=C1)C=1C=CC(=C(C=1)O)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C RFYNOSZOQAMUOK-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- APSLUPXFNWDZNC-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C(C)(C)(C)NC1CN(CC1)C1=NC=C(N=C1)C1=C(C(=C(C=C1)C=1C=NNC=1)F)F APSLUPXFNWDZNC-UHFFFAOYSA-N 0.000 claims 1
- PDIDVOFMELOGGH-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1ccc(-c2cn[nH]c2)c(F)c1F PDIDVOFMELOGGH-UHFFFAOYSA-N 0.000 claims 1
- WOIZIPCMOCBZBO-UHFFFAOYSA-N N-tert-butyl-1-[5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]pyrazin-2-yl]pyrrolidin-3-amine dihydrochloride Chemical compound Cl.Cl.CC(C)(C)NC1CCN(C1)c1cnc(cn1)-c1cc(F)c(cc1F)-c1cn[nH]c1 WOIZIPCMOCBZBO-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- QIWWIXNCPDYEJP-UHFFFAOYSA-N [2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]-5-(triazol-2-yl)phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)NC1=NC=C(N=C1)C1=C(OC=O)C=C(C=C1)N1N=CC=N1 QIWWIXNCPDYEJP-UHFFFAOYSA-N 0.000 claims 1
- FXDAWMJWIUPBSD-UHFFFAOYSA-N [5-(1-methylpyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C=1C=NN(C=1)C)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C FXDAWMJWIUPBSD-UHFFFAOYSA-N 0.000 claims 1
- UVBXTCOTFIZBHE-UHFFFAOYSA-N [5-(1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn[nH]c1 UVBXTCOTFIZBHE-UHFFFAOYSA-N 0.000 claims 1
- IBMAILOZWWNVKT-UHFFFAOYSA-N [5-(1H-pyrazol-5-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccn[nH]1 IBMAILOZWWNVKT-UHFFFAOYSA-N 0.000 claims 1
- HURNPEQOZUBPSS-UHFFFAOYSA-N [5-(4-fluoropyrazol-1-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-n1cc(F)cn1 HURNPEQOZUBPSS-UHFFFAOYSA-N 0.000 claims 1
- ZDTULKQFWWTJBO-UHFFFAOYSA-N [5-(5-fluoro-1H-pyrazol-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn[nH]c1F ZDTULKQFWWTJBO-UHFFFAOYSA-N 0.000 claims 1
- NYDUCOVDAAROBE-UHFFFAOYSA-N [5-(6-methoxypyrimidin-4-yl)-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound COc1cc(ncn1)-c1ccc(c(OC=O)c1)-c1cnc(NC2CC(C)(C)NC(C)(C)C2)cn1 NYDUCOVDAAROBE-UHFFFAOYSA-N 0.000 claims 1
- JUILYRQXBWZWDC-UHFFFAOYSA-N [5-imidazo[1,2-a]pyrazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cn2ccnc2cn1 JUILYRQXBWZWDC-UHFFFAOYSA-N 0.000 claims 1
- YJKFHESCRFFOIO-UHFFFAOYSA-N [5-imidazo[1,2-b]pyridazin-6-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccc2nccn2n1 YJKFHESCRFFOIO-UHFFFAOYSA-N 0.000 claims 1
- UOYQEAQPHOWXSJ-UHFFFAOYSA-N [5-imidazol-1-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-n1ccnc1 UOYQEAQPHOWXSJ-UHFFFAOYSA-N 0.000 claims 1
- SJHTYWAUBLWORY-UHFFFAOYSA-N [5-pyridin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccccn1 SJHTYWAUBLWORY-UHFFFAOYSA-N 0.000 claims 1
- VVHBDZBUFVONLN-UHFFFAOYSA-N [5-pyridin-3-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1cccnc1 VVHBDZBUFVONLN-UHFFFAOYSA-N 0.000 claims 1
- QPCHTSAXCSKMHV-UHFFFAOYSA-N [5-pyridin-4-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound CC1(C)CC(CC(C)(C)N1)Nc1cnc(cn1)-c1ccc(cc1OC=O)-c1ccncc1 QPCHTSAXCSKMHV-UHFFFAOYSA-N 0.000 claims 1
- VIOQLPSVXJWYCC-UHFFFAOYSA-N [5-pyrimidin-2-yl-2-[5-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]pyrazin-2-yl]phenyl] formate Chemical compound C(=O)OC1=C(C=CC(=C1)C1=NC=CC=N1)C1=NC=C(N=C1)NC1CC(NC(C1)(C)C)(C)C VIOQLPSVXJWYCC-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- XVQUOJBERHHONY-UHFFFAOYSA-N isometheptene Chemical compound CNC(C)CCC=C(C)C XVQUOJBERHHONY-UHFFFAOYSA-N 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Claims (16)
- 式(I)の化合物、またはその形態を含む化合物であって、化合物の形態が、その塩、水和物、溶媒和物、ラセミ化合物、鏡像異性体、ジアステレオ異性体、立体異性体および互変異性体形態からなる群から選択される、化合物。
(式中、
Xは、CHR1a、C=O、O、NR1bまたは結合であり、
R1aが、水素、ハロゲン、ヒドロキシル、シアノ、C1-4アルキル、重水素-C1-4アルキル、ハロ-C1-4アルキル、アミノおよびヒドロキシル-C1-4アルキルから独立して選択され、
R1bが、水素、C1-4アルキル、重水素-C1-4アルキルおよびハロ-C1-4アルキルから独立して選択され、
Bは、ヘテロシクリルであり、
ヘテロシクリルが、N、OまたはSから独立して選択される1、2または3個のヘテロ原子環員を有する飽和または部分的不飽和3~7員環の単環式、6~10員環の二環式または13~16員環の多環式環系であり、R2からそれぞれ選択される1、2、3、4または5個の置換基でそれぞれ置換されていてもよく、
R2が、ハロゲン、C1-4アルキル、重水素-C1-4アルキル、アミノ、C1-4アルキル-アミノおよび(C1-4アルキル)2-アミノから独立して選択され、
R3は、ハロゲン、ヒドロキシル、シアノ、C1-4アルキル、重水素-C1-4アルキル、ハロ-C1-4アルキル、アミノ、C1-4アルキル-アミノ、(C1-4アルキル)2-アミノ、C1-4アルコキシ、ハロ-C1-4アルコキシ、ヘテロアリール、ヘテロシクリルおよびフェニルから独立して選択され、
ヘテロアリールが、N、OまたはSから独立して選択される1、2、3または4個のヘテロ原子環員を有する3~7員環の単環式、または6~10員環の二環式環系であり、
ヘテロシクリルが、N、OまたはSから独立して選択される1、2または3個のヘテロ原子環員を有する飽和または部分的不飽和3~7員環の単環式、6~10員環の二環式または13~16員環の多環式環系であり、
フェニル、ヘテロアリールまたはヘテロシクリルの各例が、R4からそれぞれ選択される1または2個の置換基で置換されていてもよく、
nは、1、2または3であり、
R4が、ハロゲン、ヒドロキシル、シアノ、C1-4アルキル、重水素-C1-4アルキル、ハロ-C1-4アルキル、アミノ、C1-4アルキル-アミノ、(C1-4アルキル)2-アミノ、C1-4アルコキシおよびハロ-C1-4アルコキシから独立して選択される) - Xが、NR1bおよび結合から選択される、請求項1に記載の化合物。
- Bが、アゼチジニル、テトラヒドロフラニル、ピロリジニル、ピペリジニル、ピペラジニル、1,4-ジアゼパニル、1,2-ジヒドロピリジニル、1,2,5,6-テトラヒドロピリジニル、1,2,3,6-テトラヒドロピリジニル、ヘキサヒドロシクロペンタピロール-(1H)-イル、ヘキサヒドロピロロ[3,2-b]ピロール-(2H)-イル、ヘキサヒドロピロロ[3,4-b]ピロール-(2H)-イル、(3aS,6aS)-ヘキサヒドロピロロ[3,4-b]ピロール-(2H)-イル、ヘキサヒドロピロロ[3,4-b]ピロール-(1H)-イル、(3aS,6aS)-ヘキサヒドロピロロ[3,4-b]ピロール-(1H)-イル、(3aR,6aR)-ヘキサヒドロピロロ[3,4-b]ピロール-(1H)-イル、ヘキサヒドロピロロ[3,4-c]ピロール-(1H)-イル、(3aR,6aS)-ヘキサヒドロピロロ[3,4-c]ピロール-(1H)-イル、オクタヒドロ-2H-ピロロ[3,4-c]ピリジニル、オクタヒドロ-5H-ピロロ[3,2-c]ピリジニル、オクタヒドロ-6H-ピロロ[3,4-b]ピリジニル、(4aR,7aR)-オクタヒドロ-6H-ピロロ[3,4-b]ピリジニル、(4aS,7aS)-オクタヒドロ-6H-ピロロ[3,4-b]ピリジニル、ヘキサヒドロピロロ[1,2-a]ピラジン-(2H)-オン、ヘキサヒドロピロロ[1,2-a]ピラジン-(1H)-イル、(7R,8aS)-ヘキサヒドロピロロ[1,2-a]ピラジン-(1H)-イル、(8aS)-ヘキサヒドロピロロ[1,2-a]ピラジン-(1H)-イル、(8aR)-ヘキサヒドロピロロ[1,2-a]ピラジン-(1H)-イル、ヘキサヒドロ-1H-シクロブタ[1.2-c:1,4-c’]ジピロール-(3H)-イル、(8aS)-オクタヒドロピロロ[1,2-a]ピラジン-(1H)-イル、(8aR)-オクタヒドロピロロ[1,2-a]ピラジン-(1H)-イル、オクタヒドロ-2H-ピリド[1,2-a]ピラジニル、ヘキサヒドロピロロ[3,4-b][1,4]オキサジン-(2H)-イル、5-アザスピロ[2.4]ヘプタニル、2-オキサ-6-アザスピロ[3.4]オクタニル、3-アザビシクロ[3.1.0]ヘキサニル、8-アザビシクロ[3.2.1]オクタニル、(1R,5S)-8-アザビシクロ[3.2.1]オクタニル、8-アザビシクロ[3.2.1]オクタ-2-エン-イル、(1R,5S)-8-アザビシクロ[3.2.1]オクタ-2-エン-イル、9-アザビシクロ[3.3.1]ノナニル、(1R,5S)-9-アザビシクロ[3.3.1]ノナニル、2,5-ジアザビシクロ[2.2.1]ヘプタニル、(1S,4S)-2,5-ジアザビシクロ[2.2.1]ヘプタニル、1,4-ジアザビシクロ[3.1.1]ヘプタニル、3,6-ジアザビシクロ[3.2.0]ヘプタニル、2,5-ジアザビシクロ[2.2.2]オクタニル、1,4-ジアザビシクロ[3.2.1]オクタニル、3,8-ジアザビシクロ[3.2.1]オクタニル、(1R,5S)-3,8-ジアザビシクロ[3.2.1]オクタニル、1,4-ジアザビシクロ[3.2.2]ノナニル、アザスピロ[3.3]ヘプタニル、4,7-ジアザスピロ[2.5]オクタニル、2,6-ジアザスピロ[3.3]ヘプタン-2-イル、2,6-ジアザスピロ[3.4]オクタニル、1,7,-ジアザスピロ[4.4]ノナニル、1,7-ジアザスピロ[3.5]ノナニル、2,6-ジアザスピロ[3.5]ノナニル、2,7-ジアザスピロ[3.5]ノナニル、5,8-ジアザスピロ[3.5]ノナニル、2,7-ジアザスピロ[4.4]ノナニル、2,7-ジアザスピロ[4.5]デカニル、2,8-ジアザスピロ[4.5]デカニル、6,9-ジアザスピロ[4.5]デシル、および7-アザジスピロ[5.1.58.36]ヘキサデカニルから選択され、1、2、3、4または5個のR2置換基で置換されていてもよい、請求項1に記載の化合物。
- Bが、ピロリジニル、ピペリジニル、ヘキサヒドロピロロ[3,4-c]ピロール-(1H)-イル、8-アザビシクロ[3.2.1]オクタニル、2,6-ジアザスピロ[3.4]オクタニルおよび7-アザジスピロ[5.1.58.36]ヘキサデカニルから選択され、1、2、3、4または5個のR2置換基で置換されていてもよい、請求項1に記載の化合物。
- R3が、チエニル、1H-ピラゾリル、1H-イミダゾリル、1,3-チアゾリル、オキサゾリル、1,2,4-オキサジアゾリル、1,2,4-チアジアゾリル、1H-1,2,3-トリアゾリル、2H-1,2,3-トリアゾリル、1H-1,2,4-トリアゾリル、1H-テトラゾリル、2H-テトラゾリル、ピリジニル、ピリジン-2(1H)-オン-イル、ピリミジニル、ピリミジン-4(3H)-オン-イル、ピリダジニル、ピリダジン-3(2H)-オン-イル、1,2,4-トリアジニル、1,3,5-トリアジニル、1H-インドリル、1H-インダゾリル、2H-インダゾリル、インドリジニル、ベンゾフラニル、ベンゾチエニル、1H-ベンゾイミダゾリル、1,3-ベンゾオキサゾリル、1,3-ベンゾチアゾリル、1,3-ベンゾジオキソリル、1,2,3-ベンゾトリアゾリル、9H-プリニル、フロ[3,2-b]ピリジニル、フロ[3,2-c]ピリジニル、フロ[2,3-c]ピリジニル、1,3-オキサゾロ[5,4-b]ピリジニル、チエノ[3,2-c]ピリジニル、チエノ[2,3-d]ピリミジニル、1H-ピロロ[2,3-b]ピリジニル、1H-ピロロ[2,3-c]ピリジニル、ピロロ[1,2-a]ピリミジニル、ピロロ[1,2-a]ピラジニル、ピロロ[1,2-b]ピリダジニル、ピラゾロ[1,5-a]ピリジン-イル、ピラゾロ[1,5-a]ピリジニル、1H-ピラゾロ[3,4-b]ピラジニル、1H-ピラゾロ[3,4-b]ピリジニル、1H-ピラゾロ[3,4-b]ピリジニル、1H-ピラゾロ[3,4-c]ピリジニル、1H-ピラゾロ[3,4-c]ピリジニル、1H-ピラゾロ[4,3-b]ピリジニル、1H-ピラゾロ[4,3-b]ピリジニル、1H-ピラゾロ[4,3-d]ピリミジニル、2H-ピラゾロ[4,3-b]ピリジニル、2H-ピラゾロ[4,3-c]ピリジン-イル、5H-ピロロ[2,3-b]ピラジニル、ピラゾロ[1,5-a]ピラジニル、イミダゾ[1,2-a]ピリジニル、イミダゾ[1,2-a]ピリジニル、イミダゾ[1,2-a]ピリミジニル、イミダゾ[1,2-a]ピリミジニル、イミダゾ[1,2-c]ピリミジニル、イミダゾ[1,2-b]ピリダジニル、イミダゾ[1,2-b]ピリダジニル、イミダゾ[1,2-a]ピラジニル、イミダゾ[1,2-a]ピラジニル、1H-イミダゾ[4,5-b]ピリジニル、3H-イミダゾ[4,5-b]ピリジニル、イミダゾ[2,1-b][1,3]チアゾリル、イミダゾ[2,1-b][1,3,4]チアジアゾリル、[1,3]オキサゾロ[4,5-b]ピリジニル、[1,2,3]トリアゾロ[1,5-a]ピリジニル、[1,2,3]トリアゾロ[1,5-a]ピリジニル、1H-[1,2,3]トリアゾロ[4,5-b]ピリジニル、3H-[1,2,3]トリアゾロ[4,5-b]ピリジニル、テトラゾロ[1,5-a]ピリジニル、テトラゾロ[1,5-b]ピリダジニル、キノリニル、イソキノリニル、およびキノキサリニルから選択され、1または2個のR4置換基で置換されていてもよいヘテロアリールである、請求項1に記載の化合物。
- R3が、1H-ピラゾリル、1H-イミダゾリル、2H-1,2,3-トリアゾリル、1H-1,2,4-トリアゾリル、ピリジニル、ピリジン-2(1H)-オン-イル、ピリミジニル、1,3,5-トリアジニル、イミダゾ[1,2-b]ピリダジニルおよびイミダゾ[1,2-α]ピラジニルから選択され、1または2個のR4置換基で置換されていてもよいヘテロアリールである、請求項1に記載の化合物。
- 化合物の形態が、塩酸塩、臭化水素酸塩、トリフルオロ酢酸塩、ギ酸塩、二塩酸塩、三塩酸塩、四塩酸塩、二臭化水素酸塩および二トリフルオロ酢酸塩から選択される化合物塩である、請求項1に記載の化合物。
- 4-(3-ヒドロキシ-4-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェニル)ピリジン-2-オール;
5-(1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)オキシ]ピラジン-2-イル}フェノール;
2-{5-[(7-アザジスピロ[5.1.58.36]ヘキサデカン-15-イル)(メチル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
5-[2,5-ジクロロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-(1H-イミダゾール-1-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
2-[5-(ヘキサヒドロピロロ[3,4-c]ピロール-2(1H)-イル)ピラジン-2-イル]-5-(1H-ピラゾール-4-イル)フェノール;
2-{5-[(ピペリジン-4-イル)オキシ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
2-{5-[(ピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-[5-(トリフルオロメチル)-1H-ピラゾール-4-イル]フェノール;
2-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-5-[(2,2,6,6-テトラメチルピペリジン-4-イル)オキシ]ピラジン;
5-[2-フルオロ-5-メチル-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-(5-メチル-1H-ピラゾール-4-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-(3-アミノ-1H-ピラゾール-1-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-[2,5-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-[3-フルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-[3,5-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
4-(3-ヒドロキシ-4-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェニル)-1-メチルピリジン-2(1H)-オン;
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-1-イル)フェノール;
2-{5-[メチル(ピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
2-[5-(2,6-ジアザスピロ[3.4]オクタン-2-イル)ピラジン-2-イル]-5-(1H-ピラゾール-4-イル)フェノール;
4-フルオロ-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
5-[5-クロロ-2-フルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
4-フルオロ-5-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-2-(1H-ピラゾール-4-イル)ベンゾニトリル;
2-[5-(8-アザビシクロ[3.2.1]オクタ-3-イルオキシ)ピラジン-2-イル]-5-(1H-ピラゾール-4-イル)フェノール;
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
5-(1-メチル-1H-ピラゾール-4-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-[1-(2H3)メチル-1H-ピラゾール-4-イル]-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
(5-(2-ヒドロキシ-4-(1H-ピラゾール-4-イル)フェニル)ピラジン-2-イル)(2,2,6,6-テトラメチルピペリジン-4-イル)メタノン;
2-(5-(2-ヒドロキシ-4-(1H-ピラゾール-4-イル)フェニル)ピラジン-2-イル)-2-(2,2,6,6-テトラメチルピペリジン-4-イル)アセトニトリル;
2-(5-(アミノ(2,2,6,6-テトラメチルピペリジン-4-イル)メチル)ピラジン-2-イル)-5-(1H-ピラゾール-4-イル)フェノール;
2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)-5-(1,3,5-トリアジン-2-イル)フェノール;
4-(3-ヒドロキシ-4-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェニル)-1,3,5-トリアジン-2-オール;
5-(4-アミノ-1,3,5-トリアジン-2-イル)-2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェノール;
5-(4-クロロ-1,3,5-トリアジン-2-イル)-2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェノール;
5-(5-クロロ-1H-ピラゾール-4-イル)-2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェノール;
4-(3-ヒドロキシ-4-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェニル)-1H-ピラゾール-5-カルボニトリル;
5-(1,5-ジメチル-1H-ピラゾール-4-イル)-2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェノール;
5-(5-クロロ-1-メチル-1H-ピラゾール-4-イル)-2-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェノール;
4-(3-ヒドロキシ-4-(5-(メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ)ピラジン-2-イル)フェニル)-1-メチル-1H-ピラゾール-5-カルボニトリル;
5-[2,3-ジフルオロ-4-(4-メチル-1H-イミダゾール-1-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-[2,5-ジフルオロ-4-(3-メチル-1H-1,2,4-トリアゾール-1-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン;
5-(3-フルオロ-1H-ピラゾール-4-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(ピリジン-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(ピリジン-3-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(ピリミジン-2-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(ピリジン-2-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(6-メトキシピリミジン-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(1H-イミダゾール-1-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(2H-1,2,3-トリアゾール-2-イル)フェノール;
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール;
5-(イミダゾ[1,2-a]ピラジン-6-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(1-メチル-1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(1-メチル-1H-ピラゾール-3-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(イミダゾ[1,2-b]ピリダジン-6-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(5-フルオロ-1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(1H-ピラゾール-3-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
5-(4-フルオロ-1H-ピラゾール-1-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール;
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-[1-(2H3)メチル-1H-ピラゾール-4-イル]フェノール;
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(2H-1,2,3-トリアゾール-2-イル)フェノール;
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(1-メチル-1H-ピラゾール-4-イル)フェノール;
N-tert-ブチル-1-{5-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]ピラジン-2-イル}ピロリジン-3-アミン;
N-tert-ブチル-1-{5-[2,5-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]ピラジン-2-イル}ピロリジン-3-アミン;および
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(3-フルオロ-1H-ピラゾール-4-イル)フェノール
からなる群から選択される化合物であって、化合物の形態が、その塩、水和物、溶媒和物、ラセミ化合物、鏡像異性体、ジアステレオ異性体、立体異性体および互変異性体形態からなる群から選択される、化合物。 - 化合物の形態が、
5-(1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)オキシ]ピラジン-2-イル}フェノール塩酸塩、
2-[5-(ヘキサヒドロピロロ[3,4-c]ピロール-2(1H)-イル)ピラジン-2-イル]-5-(1H-ピラゾール-4-イル)フェノール四塩酸塩、
2-{5-[(ピペリジン-4-イル)オキシ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール三塩酸塩、
2-{5-[(ピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール四塩酸塩、
2-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-5-[(2,2,6,6-テトラメチルピペリジン-4-イル)オキシ]ピラジン三塩酸塩、
5-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]-N-メチル-N-(2,2,6,6-テトラメチルピペリジン-4-イル)ピラジン-2-アミン塩酸塩、
2-[5-(8-アザビシクロ[3.2.1]オクタ-3-イルオキシ)ピラジン-2-イル]-5-(1H-ピラゾール-4-イル)フェノール塩酸塩、
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール臭化水素酸塩、
5-[1-(2H3)メチル-1H-ピラゾール-4-イル]-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール二塩酸塩、
5-(3-フルオロ-1H-ピラゾール-4-イル)-2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノール二塩酸塩、
5-(ピリジン-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(ピリジン-3-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(ピリミジン-2-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(ピリジン-2-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(6-メトキシピリミジン-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(1H-イミダゾール-1-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(2H-1,2,3-トリアゾール-2-イル)フェノールギ酸塩、
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(1H-ピラゾール-4-イル)フェノール二塩酸塩、
5-(イミダゾ[1,2-a]ピラジン-6-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(1-メチル-1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(イミダゾ[1,2-b]ピリダジン-6-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(5-フルオロ-1H-ピラゾール-4-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(1H-ピラゾール-3-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
5-(4-フルオロ-1H-ピラゾール-1-イル)-2-{5-[(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}フェノールギ酸塩、
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-[1-(2H3)メチル-1H-ピラゾール-4-イル]フェノール二塩酸塩、
2-{5-[メチル(2,2,6,6-テトラメチルピペリジン-4-イル)アミノ]ピラジン-2-イル}-5-(2H-1,2,3-トリアゾール-2-イル)フェノール二塩酸塩、
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(1-メチル-1H-ピラゾール-4-イル)フェノール二塩酸塩、
N-tert-ブチル-1-{5-[2,3-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]ピラジン-2-イル}ピロリジン-3-アミン二塩酸塩、
N-tert-ブチル-1-{5-[2,5-ジフルオロ-4-(1H-ピラゾール-4-イル)フェニル]ピラジン-2-イル}ピロリジン-3-アミン二塩酸塩、および
2-{5-[3-(tert-ブチルアミノ)ピロリジン-1-イル]ピラジン-2-イル}-5-(3-フルオロ-1H-ピラゾール-4-イル)フェノール二塩酸塩
からなる群から選択される化合物塩、またはその形態であって、化合物の形態が、その塩、水和物、溶媒和物、ラセミ化合物、鏡像異性体、ジアステレオ異性体、立体異性体および互変異性体形態からなる群から選択される、請求項6に記載の化合物。 - 有効量の請求項1、8または9のいずれか1項に記載の化合物を含む、それを必要とする対象においてHDを処置または寛解するための医薬組成物。
- 化合物の有効量が、約0.001mg/kg/日~約500mg/kg/日の範囲である、請求項10に記載の医薬組成物。
- それを必要とする対象においてHDを処置または寛解するための医薬の製造における、請求項1、8または9のいずれか1項に記載の化合物の使用であって、前記医薬が有効量の前記化合物を含む、使用。
- 医薬における化合物の有効量が、約0.001mg/kg/日~約500mg/kg/日の範囲である、請求項12に記載の使用。
- それを必要とする対象においてHDを処置または寛解するための医薬組成物の調製における、請求項1、8または9のいずれか1項に記載の化合物の使用であって、前記医薬組成物が1つまたは複数の医薬として許容できる賦形剤と混和した式(I)の化合物、またはその形態の有効量を含む、使用。
- 医薬組成物における化合物の有効量が、約0.001mg/kg/日~約500mg/kg/日の範囲である、請求項14に記載の使用。
- 1つまたは複数の医薬として許容できる賦形剤と混和した、請求項1、8または9のいずれか1項に記載の化合物を含む、医薬組成物。
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2019
- 2019-03-26 WO PCT/US2019/024068 patent/WO2019191092A1/en unknown
- 2019-03-26 CN CN201980022422.XA patent/CN112135815A/zh active Pending
- 2019-03-26 KR KR1020207027340A patent/KR20210005559A/ko not_active Application Discontinuation
- 2019-03-26 CA CA3094703A patent/CA3094703A1/en active Pending
- 2019-03-26 AU AU2019243048A patent/AU2019243048A1/en active Pending
- 2019-03-26 EA EA202092001A patent/EA202092001A1/ru unknown
- 2019-03-26 US US17/040,751 patent/US20210009590A1/en active Pending
- 2019-03-26 JP JP2020552026A patent/JP7399870B2/ja active Active
- 2019-03-26 SG SG11202009212WA patent/SG11202009212WA/en unknown
- 2019-03-26 BR BR112020019373-9A patent/BR112020019373A2/pt not_active Application Discontinuation
- 2019-03-26 MX MX2020009957A patent/MX2020009957A/es unknown
- 2019-03-27 EP EP19777730.3A patent/EP3773552A4/en active Pending
- 2019-03-27 EA EA202092003A patent/EA202092003A1/ru unknown
- 2019-03-27 JP JP2020551538A patent/JP7399869B2/ja active Active
- 2019-03-27 BR BR112020019264-3A patent/BR112020019264A2/pt unknown
- 2019-03-27 SG SG11202009211VA patent/SG11202009211VA/en unknown
- 2019-03-27 MX MX2020009956A patent/MX2020009956A/es unknown
- 2019-03-27 KR KR1020207027339A patent/KR20210005558A/ko not_active Application Discontinuation
- 2019-03-27 AU AU2019243943A patent/AU2019243943A1/en active Pending
- 2019-03-27 US US17/040,104 patent/US11780839B2/en active Active
- 2019-03-27 CA CA3094700A patent/CA3094700A1/en active Pending
- 2019-03-27 WO PCT/US2019/024278 patent/WO2019191229A1/en unknown
- 2019-03-27 CN CN201980022516.7A patent/CN112203653A/zh active Pending
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2020
- 2020-09-22 IL IL277497A patent/IL277497A/en unknown
- 2020-09-22 IL IL277498A patent/IL277498A/en unknown
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2023
- 2023-06-16 US US18/211,134 patent/US20230331725A1/en active Pending
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